冈伯格かく-巴ともえ赫曼反はん应

Gomberg–Bachmann反はん应（又また称たたえ冈伯格かく-巴ともえ克かつ曼反应、冈伯格かく-巴ともえ赫曼反はん应、Gomberg芳よし基もと偶联反はん应等ひとし）以乌克かつ兰裔美国びくに化学かがく家か摩ま西にし·冈伯格かく（Moses Gomberg）和美かずみ国こく化学かがく家か沃纳·以马利り·巴ともえ赫曼（Werner Emmanuel Bachmann）的てき名字みょうじ命名めいめい^[1]^[2]^[3]，是ぜ指ゆび重じゅう氮盐的てき酸性さんせい溶液ようえき用よう氢氧化か钠或ある乙おつ酸さん钠的てき水溶液すいようえき处理时，发生芳よし基もと的てき偶联反はん应，生成せいせい联芳烃的てき衍生物的ぶってき反はん应。例れい如，对溴苯胺与あずか苯偶联，得とく到いた对溴联苯^[4]。

BrC₆H₄NH₂ + C₆H₆ → BrC₆H₄−C₆H₅

这个反はん应能应用于各种类型がた的てき芳香ほうこう环，包括ほうかつ二に茂しげる铁^[5] 和わ醌类。由よし于重氮盐能のう发生许多副ふく反はん应，因いん此反应产率りつ一いち般不高だか，通常つうじょう低てい于 40％。

Gomberg–Bachmann 反はん应的分子ぶんし内ない版本はんぽん为 Pschorr反はん应（下しも图）。^[6]^[7] 其中 Z 基もと一般いっぱん是ぜ CH₂；CH₂CH₂；NH；CO，产物为芴、芴酮和わ咔唑类化合かごう物ぶつ。^[8]

反はん应机理り[编辑]

一般いっぱん认为是ぜ自由じゆう基もと历程：

{\rm {\ C_{6}H_{5}N_{2}Cl\rightarrow C_{6}H_{5}\cdot +N_{2}+Cl\cdot }}

（均ひとし裂きれ）

{\rm {\ C_{6}H_{5}\cdot +C_{6}H_{5}NO_{2}\rightarrow {\mathit {p}}\!-\!C_{6}H_{5}\!-\!C_{6}H_{4}NO_{2}+H\cdot }}

{\rm {\ H\cdot +Cl\cdot \rightarrow HCl}}

参まいり见[编辑]

参考さんこう资料[编辑]

^ M. Gomberg, W. E. Bachmann. The Synthesis of Biaryl Compounds by Means of the Diazo Reaction. J. Am. Chem. Soc. 1924, 42: 2339–2343. doi:10.1021/ja01675a026.
^ W. Pötsch. Lexikon bedeutender Chemiker (VEB Bibliographisches Institut Leipzig, 1989) (ISBN 3817110553)
^ M. B. Smith, J. March. March's Advanced Organic Chemistry (Wiley, 2001) (ISBN 0-471-58589-0)
^ M. Gomberg and W. E. Bachmann (1941). "p-Bromobiphenyl". Org. Synth.; Coll. Vol. 1: 113.
^ D. F. DeTar, Org. Reactions, 9, 411 (1957).
^ R. Pschorr. Neue Synthese des Phenanthrens und seiner Derivate. Chem. Ber. 1896, 29 (1): 496–501. doi:10.1002/cber.18960290198.
^ March, Jerry (1985). Advanced Organic Chemistry, Reactions, Mechanisms and Structure, third Edition, John Wiley & Sons. ISBN 0-471-85472-7.
^ Stephen A. Chandler,a Peter Hanson, Alec B. Taylor, Paul H. Walton and Allan W. Timmsb. Sandmeyer reactions. Part 5.1 Estimation of the rates of 1,5-aryl/aryl radical translocation and cyclisation during Pschorr fluorenone synthesis with a comparative analysis of reaction energetics. J. Chem. Soc., Perkin Trans. 2. 2001: 214–228. doi:10.1039/b006184k.

[1] M. Gomberg, W. E. Bachmann. The Synthesis of Biaryl Compounds by Means of the Diazo Reaction. J. Am. Chem. Soc. 1924, 42: 2339–2343. doi:10.1021/ja01675a026.

[2] W. Pötsch. Lexikon bedeutender Chemiker (VEB Bibliographisches Institut Leipzig, 1989) (ISBN 3817110553)

[3] M. B. Smith, J. March. March's Advanced Organic Chemistry (Wiley, 2001) (ISBN 0-471-58589-0)

[4] M. Gomberg and W. E. Bachmann (1941). "p-Bromobiphenyl". Org. Synth.; Coll. Vol. 1: 113.

[5] D. F. DeTar, Org. Reactions, 9, 411 (1957).

[6] R. Pschorr. Neue Synthese des Phenanthrens und seiner Derivate. Chem. Ber. 1896, 29 (1): 496–501. doi:10.1002/cber.18960290198.

[7] March, Jerry (1985). Advanced Organic Chemistry, Reactions, Mechanisms and Structure, third Edition, John Wiley & Sons. ISBN 0-471-85472-7.

[8] Stephen A. Chandler,a Peter Hanson, Alec B. Taylor, Paul H. Walton and Allan W. Timmsb. Sandmeyer reactions. Part 5.1 Estimation of the rates of 1,5-aryl/aryl radical translocation and cyclisation during Pschorr fluorenone synthesis with a comparative analysis of reaction energetics. J. Chem. Soc., Perkin Trans. 2. 2001: 214–228. doi:10.1039/b006184k.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]